Contacting ex-colleague I like

[Broonie71]

Hi,

I am hoping someone can provide some advice.

I recently found out an ex-colleague whom I like is newly single, and I'd like to get in touch with her, and ask her out. We no longer work in the same company and our paths rarely cross. The last time was 3 years ago at an ex-colleagues funeral (when she was in a relationship). Anyway, I was thinking of sending her the text below. Does this come across as desperate, creepy or will it scare her off, or does it come across as a casual (not sexual) "lets meet" type of thing. 

Note: I'm also on the spectrum, and find these things awkward at the best of time, and I have little confidence. 

I also have little expectation of meeting her following the text below as she has 2 teenage kids which she will probably need to do stuff with on the day I'm suggesting.

Any constructive feedback is appreciated.

Text below.

---------------------------------------

Hi <insert name>,

Long time no speak - hope you are well.

I know this message is out of the blue however I'm going to be in <insert town where she lives> next Saturday as my car is undergoing some minor repairs at a local garage. Anyway I plan to pass the time waiting for the repairs to complete in Costa - so I dont look like "Billy No Mates" are you free to grab a coffee?  No worries if not as I know its the weekend and I'm sure you've got a million and 1 things you need to do with the kids.

 

[Ami1uwant]

How “ new” is she? And do you want to be a rebound?

 

just start a basic conversation with her and see how it goes before you even get to …I’ll bein town portion

[Broonie71]

Thanks for the fast response. I thought of just asking her "Hey there hows it going, whats new??" but as I hadnt spoken to her in nearly 3 years, asking her that out of the blue seemed weird. So coming up with a reason to be in her town seemed more plausible. 

[Johnjohnson2017]

That's too forthcoming for someone you haven't seen in three years.

Start slow. See if she responds back, if she's showing enthusiasm.

It's too soon to ask her out. She might not even be interested in you. Start with "Hi, It's been a long time since we spoke. How have you been doing?" Then wait for her response. Don't ask her out until a few days later (or don't ask her out if she doesn't seem interested)

[Broonie71]

Thanks - great advice.

[Versacehottie]

I also basically like the idea of starting slow if you haven't spoken in 3 years, she just is newly single, and you don't feel particularly confident.  Not to mention that contacting her will come out of the blue from her perspective. 

2 hours ago, Broonie71 said:

Hi <insert name>,

Long time no speak - hope you are well.

I know this message is out of the blue however I'm going to be in <insert town where she lives> next Saturday as my car is undergoing some minor repairs at a local garage. Anyway I plan to pass the time waiting for the repairs to complete in Costa - so I dont look like "Billy No Mates" are you free to grab a coffee?  No worries if not as I know its the weekend and I'm sure you've got a million and 1 things you need to do with the kids.

I struck out parts of your message....whether this comes out over the course of a handful of text messages on one day or over a period of time, I wouldn't recommend saying the parts I struck out...will explain.

I know this message is out of the blue however I'm going to be in <insert town where she lives>:  You are already shooting yoruself in the foot and giving excuses for why in the general scheme of things you "should not" have permission (of sorts) TO contact her. Don't worry if she feels that it's out of the blue. The long time, no speaks already takes care of that part. Also much less timid to just say something like: 

Hi (name),

Long time, no speak--Was thinking about you just today as I'm headed your way--getting my car fixed in your town in a few days (in the way you speak, doesn't have to be this speaking voice). How have you been? (open-ended question, drives conversation forward, shows care, lets her talk about herself, will give you some clues usually about what's going on with her).

Secondly: assuming the texting conversation continues, and at some point, you get to suggest meeting up: so I dont look like "Billy No Mates" are you free to grab a coffee?....IMO, don't say this--you don't need to have an excuse to see her that is filling time or any sort of obligation/responsibility at all. Just the fact that you are thinking about her, she crossed your mind is enough. Far more confident & positive to convey it that way (vs. an excuse that comes off putting yourself down). The theme should be: I have good, fun feelings when I think about you, and enjoy your company--that's sufficient. Obviously don't say these words but that's the vibe to convey. 

So assuming the texting goes on a bit, when the moment is right or even the day you are in her town:

"We should grab a coffee if you are free"...IMO, in the short term it doesn't even matter if you ask spontaneously on the day that you are in the town and then she can't make it that day. It sets it up where then you can make arrangements for another day to "catch up". If/when she says, no...then you can say "no worries, we should do it sometime soon; it'd be great to see you". 

if not as I know its the weekend and I'm sure you've got a million and 1 things you need to do with the kids. Eh, I wouldn't recommend saying this, you don't want to provide excuses for a girl to say no to your invite. A) it's the opposite of confident; your mindset has to presume that she would want to go and it's just a matter of scheduling it B) it's both timid and presumptive to provide an excuse for her before she even has a chance to respond.  I think it's best to not try to fill in the blanks for people, but to ask questions instead.  It will most likely make her feel more "seen" and connected to you, if there is a chance for things to go that way, ie if she is attracted to you. 

Lastly, try not to be overly logic with bundling the car repair trip and seeing her. I mean if you are really into her, I would fudge the actual drop off and pick up time of the car to suit the time at which she can meet. Don't overdo it. But if you are texting, don't have a hardline, well I will drop off the car at 9:00am or whatever; I think most guys with game that are into a girl will sort of pretend time is loose or not set to see if they could make both things work. haha you can't let on that you are doing this, of course. And I'm not explaining it well. But if in your shoes that's what I would do...(which btw I'm a girl so not in your shoes--but yes guys do that).

Ok good luck! hope it goes well!

 

 

Edited June 15, 2022 by Versacehottie

[Broonie71]

Thanks Versacehottie - its good to get a female perspective also. Great advice from you. Thanks..... 

I've now joined Match.com and coincidentally found her. I'm not going to get in touch via Match however....will take your advice.

Edited June 15, 2022 by Broonie71

[Versacehottie]

2 hours ago, Broonie71 said:

Thanks Versacehottie - its good to get a female perspective also. Great advice from you. Thanks..... 

I've now joined Match.com and coincidentally found her. I'm not going to get in touch via Match however....will take your advice.

Yeah, I wouldn't get in touch with her via match. You already have a better in a hierarchy sense level of potential contact with her (no need to go backward)..IMO, that might just read as "i was perusing match, and she is single and I'm single"...generally people like to feel like there is something unique and special about themselves that is drawing you to her/him. (Actually probably plays into a lot of the failure and burnout represented by dating app usage, ie no one wants to feel like they are simply being chosen because they are both in a "single" state; also being seen as single and on an site or app sort of discounts what a person truly offers, sorry just a behavioral science thing not the truth)...So meaning I would use other means of contact if available to you. That said, if she matches you on the site, you should definitely reply!

I would caution you about seeing her on match.com and drawing conclusions about her real openness for a serious relationship. Maybe it's the last thing she wants after her breakup; maybe she is just testing the waters. Another reason why the softer sell of just simply reconnecting is better IMO. No need to rush things into failure because of a hard sell. . Also if she is truly busy with her life and the life of having teenagers, you've sort of got to leave open the possibility that her feelings may take time to develop just due to logistics of what sort of time she has to date.  Anyway that's a little ways off. I'm sure if you keep posting in this thread people can and will help you. And I guess on that note, even while we are doing that, I would still rely on your own instincts, or at least express them here to get some feedback....in a way, there's no one that knows you and this woman better than you do. While you will likely get good advice, like the others gave already as well, no one person's idea is exactly gospel or a guarantee to work. Sometimes you will see lots of conflicting opinions and it will confuse you! I'd just sort of use it as a guide and definitely if there is a preponderance of similar opinions, i'd weight that heavier....like in this case, the general idea of going a bit slower with this one. (one reason why has nothing to do with either you or her--just that it truly is out of the blue!)...Ok good luck.

Edited June 15, 2022 by Versacehottie

[Ami1uwant]

3 hours ago, Broonie71 said:

Thanks Versacehottie - its good to get a female perspective also. Great advice from you. Thanks..... 

I've now joined Match.com and coincidentally found her. I'm not going to get in touch via Match however....will take your advice.

Are you thinking she’s single because of match profile???  Thus is unreliable.  There are many dead/ unused profiles on there.  It does not mean she’s active and looking.

do you have common friends?

 

 

 

 

 

 

 

[Broonie71]

3 hours ago, Ami1uwant said:

Are you thinking she’s single because of match profile???  Thus is unreliable.  There are many dead/ unused profiles on there.  It does not mean she’s active and looking.

do you have common friends?

 

 

 

 

 

 

 

No. I also see her status on Facebook has changed recently to single. 

[Wiseman2]

13 hours ago, Broonie71 said:

Ive now joined Match.com and coincidentally found her. I'm not going to get in touch via Match however

Ok. Then contact her on Match. You already have something in common so a first message on Match would be easy.  Getting in touch through appropriate means may work in your favor.

[Esther_lib]

16 hours ago, Broonie71 said:

Hi,

I am hoping someone can provide some advice.

I recently found out an ex-colleague whom I like is newly single, and I'd like to get in touch with her, and ask her out. We no longer work in the same company and our paths rarely cross. The last time was 3 years ago at an ex-colleagues funeral (when she was in a relationship). Anyway, I was thinking of sending her the text below. Does this come across as desperate, creepy or will it scare her off, or does it come across as a casual (not sexual) "lets meet" type of thing. 

Note: I'm also on the spectrum, and find these things awkward at the best of time, and I have little confidence. 

I also have little expectation of meeting her following the text below as she has 2 teenage kids which she will probably need to do stuff with on the day I'm suggesting.

Any constructive feedback is appreciated.

Text below.

---------------------------------------

Hi <insert name>,

Long time no speak - hope you are well.

I know this message is out of the blue however I'm going to be in <insert town where she lives> next Saturday as my car is undergoing some minor repairs at a local garage. Anyway I plan to pass the time waiting for the repairs to complete in Costa - so I dont look like "Billy No Mates" are you free to grab a coffee?  No worries if not as I know its the weekend and I'm sure you've got a million and 1 things you need to do with the kids.

 

I would say start out by greeting her and asking if she still remembers you. Then connect with her about how she's doing if she still remembers you. I would not advise asking someone out this quickly.

[glows]

This is not such a big deal. Just say you’re in the area and would like to catch up for coffee. You’re overthinking this. Leave out the details about your car repairs. She doesn’t need to know that/none of her business.

[Alpacalia]

20 hours ago, Johnjohnson2017 said:

That's too forthcoming for someone you haven't seen in three years.

Start slow. See if she responds back, if she's showing enthusiasm.

It's too soon to ask her out. She might not even be interested in you. Start with "Hi, It's been a long time since we spoke. How have you been doing?" Then wait for her response. Don't ask her out until a few days later (or don't ask her out if she doesn't seem interested)

I like this advice.

If I was in your shoes, I would do this as well.

 

Edited June 16, 2022 by Alpacalia

[Broonie71]

Thanks All... I am overthinking this however thats my nature. The more I think about this, the less confident I am she'll a) respond to the original text, and if she does b) agree to grab a coffee... I'll probably hold off for a month  or 2 and see how the land lies then. If she gets "snapped up" in that time then so be it. I'll probably get "friend-zoned" anyway, which is what usually happens to me lol... I'm 50 (she's early-mid 40's) and I'm hopeless at this...lol

Edited June 16, 2022 by Broonie71

[Wiseman2]

On 6/15/2022 at 1:51 PM, Broonie71 said:

I recently found out an ex-colleague whom I like is newly single, and I'd like to get in touch with her, and ask her out. We no longer work in the same company and our paths rarely cross. The last time was 3 years ago

How did you discover she is single? Are you following her social media or was it from the dating app?

You were colleagues, so are you connected on LinkedIn? Try that.

Send a friend/follow request on social media.

Contact her on Match. 

You have several avenues to break the ice and catch up. 

Sending a text for a specific time out of the blue is too much too soon.

Once you get some contact, request a mutually convenient time/place to catchup over coffee/a drink and feel out the situation that way.

 

Edited June 16, 2022 by Wiseman2

[Versacehottie]

4 minutes ago, Broonie71 said:

Thanks All... I am overthinking this however thats my nature. The more I think about this, the less confident I am she'll a) respond to the original text, and if she does b) agree to grab a coffee... I'll probably hold off for a month  or 2 and see how the land lies then. If she gets "snapped up" in that time then so be it. I'll probably get "friend-zoned" anyway, which is what usually happens to me lol...

oh no, well you need to work on your confidence. Try to "lower the stakes"...in other words, don't think of wanting her to become your gf, just that she could be a friend and you enjoy being around her.  That should raise your confidence if you CHANGE YOUR INTENTION. 

Bolded try not to think in all or nothing terms. Maybe you get friend-zoned because you don't have enough practice? If anything, this girl provides "practice" even if it does not turn into a dating relationship. Maybe you partially get friend zoned because you overthink things? Being interested in her and just leaping in a way, is a chance to do things differently. You just need to see it that way. 

I don't think you should wait it out a month or two. That's just another form of overthinking where your mind thinks it's come up with the best solution. You will still likely be in this headspace in a couple of months because nothing will have changed for you/inside of you. Better to not have regret...which is a confidence-building exercise in itself. 

if you really want to lower the stakes and start up a current friendship that could turn into something more. Just get your car fixed as planned and while you are in her town, send her a text  that basically says something to the effect that she crossed your mind since you are in her area and ask how she is. That way it's grounded in reality and genuineness and is not that calculated because you are literally getting your car fixed down the street. Try to then keep the friendship conversation going.  And whenever I say friendship, I mean (can mean) flirty friendship, if that's natural to you. Listen, guys with game absolutely realize this is a way to get their "foot in the door". They are not worried about being friend zoned by starting out with a friendly conversation. Inherent in that is the built up confidence that "if she knows me and we feel sparks and both of are still single, I'm thinking things will happen romantically between us, because why not?"  Also I would never underestimate the value of approaching a girl this way, especially if it is sort of out of the blue. 

Here's my question about you guys being friends on FB (is that the term, I'm not a FB person)...is it at an extreme distance where effectively she might not really know you exist or might not remember who you are...if so, I can see why this would being creating anxiety for you.  I'm assuming you have her phone number to text so you at one point when working together were closer than that very distant example. 

It really is about your attitude in how you approach things. If you BELIEVE, the contact will be welcome, it will. If you approach it as old friends from work, of course the contact will be welcome.  If you dial it down to that you will do better all the way around (and not come off awkward like you have to lay out your whole plan for being in her life--that's overwhelming and why it probably wouldn't go well, would come out of the blue and is a lot of pressure on both of you.)  I mean even work friends have social and work updates, who knows you could just be after industry gossip/information that would help your career or after some info where you have an opportunity for you. Those are all possible (good) reactions that she might reason why you are in touch. Just keep it basic. and hopefully you can create momentum and some traction with her in those first couple of texts. Bring enthusiasm, some joy, some umph from your banter or convo...don't be too basic or robotic but just inject fun. It's harmless to contact a former co-worker. I can barely think of a situation where it would go wrong. You just can't jump to the end with what you "want" from it. That's a lot of pressure.

[Broonie71]

We're connected on Facebook & LinkedIn, and have been for years. We dont have any mutual friends as such, and occasionally (every 3-4 years) bump into one another....

[mark clemson]

Quote

so I dont look like "Billy No Mates" 

IMO never say stuff like this. If she wants you to be interested in her, she'll want you to be interested in her for her sake. The above makes it sound like you're meeting her to "manage other's perceptions of you" which should be irrelevant. It's ok to be interested in her for romantic purposes. If she doesn't have interest in giving you a try, she will let you know.

It's hard when you're youngish (e.g. 20's and 30's) but I think women prefer a guy who looks good and yet seems to not care what anyone else thinks of him (within reason). That shows confidence and independence, which women tend to find attractive. However it can be a fine line, so I could see if one is ASD how this might be tricky.

You might try reading "A Billion Wicked Thoughts" which is a book on human sexuality. It's a long read, but you can focus on the chapters on what women find attractive (much of which is IMO misconstrued, by the pickup-artist industry). You might find having a bigger picture understanding helpful.

If you like her specifically, that is one thing. If you would just like to find a decent partner, and are open to others, then IF you are able to turn what they wrote in ABWT into actionable principles and act on them, it might help you immensely (from a statistical perspective).

Edited June 16, 2022 by mark clemson

[Ami1uwant]

8 minutes ago, Broonie71 said:

We're connected on Facebook & LinkedIn, and have been for years. We dont have any mutual friends as such, and occasionally (every 3-4 years) bump into one another....

If you are friends on those sites, have you comment on a FB posting you see?

[glows]

36 minutes ago, Broonie71 said:

Thanks All... I am overthinking this however thats my nature. The more I think about this, the less confident I am she'll a) respond to the original text, and if she does b) agree to grab a coffee... I'll probably hold off for a month  or 2 and see how the land lies then. If she gets "snapped up" in that time then so be it. I'll probably get "friend-zoned" anyway, which is what usually happens to me lol... I'm 50 (she's early-mid 40's) and I'm hopeless at this...lol

Why hold off for a month? I don’t understand what’s the issue here. It’s just coffee and people meet people every day. I think you’re your own worst enemy here. Give it a try and see how it goes.

If you don’t think you want to see her, there’s not much anyone can help you with. I agree with the previous comment about working on your confidence.

[Broonie71]

Yes I sometimes comment on her posts etc but nothing flirtatious obvs. 

I am my own worse enemy so I agree with you on that. You are right that its just coffee, and I'm overthinking etc. Nothing ventured I suppose. I'll (over)think about it over the weekend (busy so cant do it this weekend) and see how it goes.

Even though I said I'm on the spectrum, I've not been formally diagnosed with ASD (assessment pending) although I display alot of the characteristics. 

Great advice from all. Thanks.

Edited June 16, 2022 by Broonie71

[glows]

5 minutes ago, Broonie71 said:

Yes I sometimes comment on her posts etc but nothing flirtatious obvs. 

I am my own worse enemy so I agree with you on that. You are right that its just coffee, and I'm overthinking etc. Nothing ventured I suppose. I'll (over)think about it over the weekend (busy so cant do it this weekend) and see how it goes.

Even though I said I'm on the spectrum, I've not been formally diagnosed with ASD (assessment pending) although I display alot of the characteristics. 

Great advice from all. Thanks.

Remember if she doesn’t want to spend time with you or isn’t interested in catching up, it’s not your problem. You tried and if it doesn’t work out, life goes on. You can meet other women locally and enjoy your time with people who also enjoy your company.

[Versacehottie]

7 minutes ago, Broonie71 said:

Yes I sometimes comment on her posts etc but nothing flirtatious obvs. 

I am my own worse enemy so I agree with you on that. You are right that its just coffee, and I'm overthinking etc. Nothing ventured I suppose. I'll (over)think about it over the weekend (busy so cant do it this weekend) and see how it goes.

Even though I said I'm on the spectrum, I've not been formally diagnosed with ASD (assessment pending) although I display alot of the characteristics. 

Great advice from all. Thanks.

I would just also encourage you DO vs THINK (ie overthink).  There is a benefit to "doing" if someone has the tendency to overthink. You could even practice (in a way) by flirting with someone on match.com or out in person today or tomorrow with no real purpose to it other than flirt, feel good yourself and make the other person feel good. That sort of doing should get you more comfortable to bring yourself to someone, like this woman, who you really care about or where the stakes are higher. You can't really expect to go from 0-60, if you don't sort of train that socializing muscle and you can't "think" your way out of it or "think" your way through all the practice you need in just a real world situation. Also with a tendency to overthink, doing so just fuels more overthinking, strategizing etc when you really just have to "just do it". It's like strengthening a muscle which needs reps/being under pressure to grow and perform better. 

You can't replicate real world conditions to the extent that they will exist in your head.  In fact, the mind of an over thinker will come up with plenty of fears that don't even matter and will just affect how you approach the situation, which then you BRING to the situation when you eventually try, then fail or sort of fail, and it becomes a negative feedback loop. Your mindset will affect things as much as anything so you can't really hide your thoughts because they typically slip out in between the lines of a text, a conversation or your actions.An overthinker tends to plan out the conversation or set of actions like the perfect formula of those ingredients will determine success or failure...rather than gaining real actual experience of trying failing and not seeing it as a big deal or entirely dependent on only you (variety of factors, lots not within your control and that you can never anticipate or out-strategize),,,so you probably are at the threshold where the volume/quality of the experience will net you more positive gains than more personal and private thinking (including polling/asking advice of us anonymous people).

 

[Wiseman2]

52 minutes ago, Broonie71 said:

We're connected on Facebook & LinkedIn, and have been for years.

Ok, great just send a friendly, "how are you?" type of message and take it from there.